Manager Mauricio Pochettino was brought into White Hart Lane with the task of breaking Tottenham into the top four.
But wild spending by former managers who were attempting this same feat has left the club with a lot of deadwood. There are too many players on Spurs’ books that have been underperforming for far too long and come the summer transfer window, Pochettino needs to get rid of as many as possible.
It is only thanks to outstanding players like Harry Kane, who is in contention for being the league's top goal scorer, why the Spurs have even placed as high as sixth.
Pochettino has had a whole year to figure out which players can help Spurs climb the table next season and these five have proven that they are not up to the task...
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Roberto Soldado
The Spaniard joined Spurs in 2013, signing a four year contract worth £26 million. But he has failed to earn that considerable wage, scoring only seven league goals throughout his two seasons at the club.
The situation at White Hart Lane doesn’t look like improving as the forward has been given only seven starts under Pochettino, so he doesn’t appear to be a part of the club's future plans.
Selling the player just two years after purchasing him and with his performances having been so dire means that the club will probably make a big loss, but at least they’ll be rid of him.
Erik Lamela
The attacking midfielder has made a very limited impact since his arrival in north London two seasons ago.
In his 28 league appearances for Tottenham, Lamela has scored just the once had has never really adapted to the English game. Lamela was Spurs’ highest paid signing when he arrived, but as with Soldado, the club are unlikely to make their money back when selling him on.
Previously the 23-year-old had a successful spell at Roma, so perhaps a return to Italy would be a good way to rejuvenate his career while he is still young.
Emmanuel Adebayor
Adebayor has been in and out of favour during his four years at the club, but his time may finally be up this summer.
The Togo international joined Spurs under manager Harry Redknapp - initially on a year-long loan deal - in which he scored an impressive 17 goals from 33 appearances.
The club then signed him permanently but his form and eye for goal both dropped considerably. At 31-years-old, Adebayor is unlikely to improve to a high enough level so it is best to flog him now if they can.
Paulinho
Once described as a powerful box-to-box midfielder, the Brazilian is yet another example of a player who has spent the entirety of his career at Spurs struggling to adapt.
Signed for £17million two years ago, the arrival of Paulinho created a buzz around White Hart Lane as the midfielder had just won the Copa Libertadores and FIFA Club World Cup with his former team Corinthians.
But the 26-year-old just can’t seem to recreate his once impressive form for Spurs and even though he has shown minor improvement recently, it is still not enough to warrant holding onto him.
Vlad Chiriches
The Romanian centre-back is another player from the class of 2013 who was signed as manager Andre Villas-Boas set about rebuilding a Spurs team worthy of a top four finish.
Chiriches' first season at the club saw him make 17 league appearances, but this time around he has featured on only eight occasions.
At the end of the last winter transfer window Italian side Roma offered to take Chiriches on a six month loan but their final offer was deemed too low and so the defender remained in north London.
Since then he has had few opportunities to impress and is unlikely to receive many more if he does stay at Tottenham next season.